Hydrochloric Acid → HCID 86715340, compound

Temperature

0 °C

To a cooled (0° C.) suspension of (methoxymethyl)triphenylphosphonium chloride (155 g, 452 mmol) in THF (700 mL) was added potassium tert-butoxide (1.0 M in THF, 452 mL, 452 mmol) at such a rate that the internal temperature did not exceed 7° C. The mixture was stirred for 1 hour at 0° C., and then a solution of ethyl 2-methyl-4-oxocyclohexanecarboxylate (64 g, 347 mmol) in THF (150 mL) was added via canula at such a rate that the internal temperature did not exceed 7° C. The mixture was then slowly warmed to room temperature and stirred for 14 hours. The reaction mixture was then cooled to 10° C. and diluted with water (200 mL) followed by 6 M HCl (500 mL). The resulting mixture was stirred for 3 hours, and then diluted with additional water (400 mL) and EtOAc (700 mL). The organic layer was separated, and the aqueous layer was extracted a second time with EtOAc (700 mL). The organic layers were combined, dried over MgSO4, filtered, absorbed on silica gel, and purified by silica gel chromatography to afford ethyl 4-formyl-2-methylcyclohexanecarboxylate, which was used immediately in the subsequent step.

1. temperatureTo a cooled
2. customdid not exceed 7° C
3. customdid not exceed 7° C
4. temperatureThe mixture was then slowly warmed to room temperature
5. stirringstirred for 14 hours
6. temperatureThe reaction mixture was then cooled to 10° C.
7. stirringThe resulting mixture was stirred for 3 hours
8. customThe organic layer was separated
9. extractionthe aqueous layer was extracted a second time with EtOAc (700 mL)
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. customabsorbed on silica gel
13. custompurified by silica gel chromatography

ORD record

ord-f14ad8a0737f430f9e24796af168751a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120785B2